CS216221B2 - Insecticide means and method of making the active substance - Google Patents
Insecticide means and method of making the active substance Download PDFInfo
- Publication number
- CS216221B2 CS216221B2 CS803122A CS312280A CS216221B2 CS 216221 B2 CS216221 B2 CS 216221B2 CS 803122 A CS803122 A CS 803122A CS 312280 A CS312280 A CS 312280A CS 216221 B2 CS216221 B2 CS 216221B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- ylidene
- dihydrothiazol
- formula
- methylphenyl
- oxo
- Prior art date
Links
- 239000002917 insecticide Substances 0.000 title abstract description 3
- 239000013543 active substance Substances 0.000 title description 9
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 alkali metal salt Chemical class 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 230000000749 insecticidal effect Effects 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000005059 halophenyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 26
- 230000000694 effects Effects 0.000 abstract description 9
- 241000238631 Hexapoda Species 0.000 abstract description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000007921 spray Substances 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 5
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229930016911 cinnamic acid Natural products 0.000 description 3
- 235000013985 cinnamic acid Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- NUVDVYRBDIOXRJ-UHFFFAOYSA-N 2-[4-(2-methylphenyl)-1,3-thiazol-2-yl]acetonitrile Chemical compound CC1=CC=CC=C1C1=CSC(CC#N)=N1 NUVDVYRBDIOXRJ-UHFFFAOYSA-N 0.000 description 2
- BHPYMZQTCPRLNR-UHFFFAOYSA-N 2-cyanoethanethioamide Chemical compound NC(=S)CC#N BHPYMZQTCPRLNR-UHFFFAOYSA-N 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- WZXRPDNMKGXBKU-UHFFFAOYSA-N 3-(2-methylphenyl)-2-(5-methyl-4-phenyl-3h-1,3-thiazol-2-ylidene)-3-oxopropanenitrile Chemical compound S1C(C)=C(C=2C=CC=CC=2)NC1=C(C#N)C(=O)C1=CC=CC=C1C WZXRPDNMKGXBKU-UHFFFAOYSA-N 0.000 description 2
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 2
- 240000003259 Brassica oleracea var. botrytis Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000500437 Plutella xylostella Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- VTJMSIIXXKNIDJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutyric acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(Cl)C=C1 VTJMSIIXXKNIDJ-UHFFFAOYSA-N 0.000 description 1
- UQISVQVOVFZPGU-UHFFFAOYSA-N 2-(4-tert-butyl-1,3-thiazol-2-yl)acetonitrile Chemical compound CC(C)(C)C1=CSC(CC#N)=N1 UQISVQVOVFZPGU-UHFFFAOYSA-N 0.000 description 1
- UYKNWJQVKVCCIQ-UHFFFAOYSA-N 2-(4-tert-butyl-3h-1,3-thiazol-2-ylidene)-3-(2-chlorophenyl)-3-oxopropanenitrile Chemical compound N1C(C(C)(C)C)=CSC1=C(C#N)C(=O)C1=CC=CC=C1Cl UYKNWJQVKVCCIQ-UHFFFAOYSA-N 0.000 description 1
- DXARVPLVSAIPOK-UHFFFAOYSA-N 2-(4-tert-butyl-3h-1,3-thiazol-2-ylidene)-3-oxo-3-[2-(trifluoromethyl)phenyl]propanenitrile Chemical compound N1C(C(C)(C)C)=CSC1=C(C#N)C(=O)C1=CC=CC=C1C(F)(F)F DXARVPLVSAIPOK-UHFFFAOYSA-N 0.000 description 1
- KSUYJGJINOBZNY-UHFFFAOYSA-N 2-(5-bromo-4-phenyl-3h-1,3-thiazol-2-ylidene)-3-(2-chlorophenyl)-3-oxopropanenitrile Chemical compound ClC1=CC=CC=C1C(=O)C(C#N)=C1SC(Br)=C(C=2C=CC=CC=2)N1 KSUYJGJINOBZNY-UHFFFAOYSA-N 0.000 description 1
- XLZWYLLECAAHIU-UHFFFAOYSA-N 2-[4-(2-chlorophenyl)-3h-1,3-thiazol-2-ylidene]-3-oxo-3-phenylpropanenitrile Chemical compound ClC1=CC=CC=C1C(N1)=CSC1=C(C#N)C(=O)C1=CC=CC=C1 XLZWYLLECAAHIU-UHFFFAOYSA-N 0.000 description 1
- GFNAJZAKJGKJCS-UHFFFAOYSA-N 2-chloro-6-fluorobenzoyl chloride Chemical compound FC1=CC=CC(Cl)=C1C(Cl)=O GFNAJZAKJGKJCS-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- KECQUMXJWXAMPD-UHFFFAOYSA-N 3-(2-bromophenyl)-2-[4-(2-methylphenyl)-3h-1,3-thiazol-2-ylidene]-3-oxopropanenitrile Chemical compound CC1=CC=CC=C1C(N1)=CSC1=C(C#N)C(=O)C1=CC=CC=C1Br KECQUMXJWXAMPD-UHFFFAOYSA-N 0.000 description 1
- OAQHSVDPXGIVIF-UHFFFAOYSA-N 3-(2-chloro-6-fluorophenyl)-2-[4-(2-methylphenyl)-3h-1,3-thiazol-2-ylidene]-3-oxopropanenitrile Chemical compound CC1=CC=CC=C1C(N1)=CSC1=C(C#N)C(=O)C1=C(F)C=CC=C1Cl OAQHSVDPXGIVIF-UHFFFAOYSA-N 0.000 description 1
- CRHSNTJEBKHSNH-UHFFFAOYSA-N 3-(2-chlorophenyl)-2-[4-(2-chlorophenyl)-3h-1,3-thiazol-2-ylidene]-3-oxopropanenitrile Chemical compound ClC1=CC=CC=C1C(=O)C(C#N)=C1SC=C(C=2C(=CC=CC=2)Cl)N1 CRHSNTJEBKHSNH-UHFFFAOYSA-N 0.000 description 1
- QYXYIHPHJILFDU-UHFFFAOYSA-N 3-(2-chlorophenyl)-2-[4-(2-fluorophenyl)-3h-1,3-thiazol-2-ylidene]-3-oxopropanenitrile Chemical compound FC1=CC=CC=C1C(N1)=CSC1=C(C#N)C(=O)C1=CC=CC=C1Cl QYXYIHPHJILFDU-UHFFFAOYSA-N 0.000 description 1
- GMFPOXMOLKOSIL-UHFFFAOYSA-N 3-(2-chlorophenyl)-2-[4-(2-methylphenyl)-3h-1,3-thiazol-2-ylidene]-3-oxopropanenitrile Chemical compound CC1=CC=CC=C1C(N1)=CSC1=C(C#N)C(=O)C1=CC=CC=C1Cl GMFPOXMOLKOSIL-UHFFFAOYSA-N 0.000 description 1
- FZJPFKYFFIDEEE-UHFFFAOYSA-N 3-(2-chlorophenyl)-2-[4-(3-methylphenyl)-3h-1,3-thiazol-2-ylidene]-3-oxopropanenitrile Chemical compound CC1=CC=CC(C=2NC(SC=2)=C(C#N)C(=O)C=2C(=CC=CC=2)Cl)=C1 FZJPFKYFFIDEEE-UHFFFAOYSA-N 0.000 description 1
- BVJDGVOWYJCWHQ-UHFFFAOYSA-N 3-(2-chlorophenyl)-3-oxo-2-(4-pyridin-2-yl-3h-1,3-thiazol-2-ylidene)propanenitrile Chemical compound ClC1=CC=CC=C1C(=O)C(C#N)=C1SC=C(C=2N=CC=CC=2)N1 BVJDGVOWYJCWHQ-UHFFFAOYSA-N 0.000 description 1
- SJHIEFJJZMPLGG-UHFFFAOYSA-N 3-(2-fluorophenyl)-2-[4-(2-methylphenyl)-3h-1,3-thiazol-2-ylidene]-3-oxopropanenitrile Chemical compound CC1=CC=CC=C1C(N1)=CSC1=C(C#N)C(=O)C1=CC=CC=C1F SJHIEFJJZMPLGG-UHFFFAOYSA-N 0.000 description 1
- FKAQOAJUJJZESM-UHFFFAOYSA-N 3-(2-methoxyphenyl)-2-[4-(2-methylphenyl)-3h-1,3-thiazol-2-ylidene]-3-oxopropanenitrile Chemical compound COC1=CC=CC=C1C(=O)C(C#N)=C1SC=C(C=2C(=CC=CC=2)C)N1 FKAQOAJUJJZESM-UHFFFAOYSA-N 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000255579 Ceratitis capitata Species 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- IKASDZPCZZVXOP-UHFFFAOYSA-N ClC1=C(C=CC=C1)C(C(C#N)=C1SC=C(N1)C=1SC=CC1)=O Chemical compound ClC1=C(C=CC=C1)C(C(C#N)=C1SC=C(N1)C=1SC=CC1)=O IKASDZPCZZVXOP-UHFFFAOYSA-N 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- RDYMFSUJUZBWLH-UHFFFAOYSA-N endosulfan Chemical compound C12COS(=O)OCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl RDYMFSUJUZBWLH-UHFFFAOYSA-N 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792920183 DE2920183A1 (de) | 1979-05-17 | 1979-05-17 | Thiazolyliden-oxo-propionitrile, insektizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS216221B2 true CS216221B2 (en) | 1982-10-29 |
Family
ID=6071133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS803122A CS216221B2 (en) | 1979-05-17 | 1980-05-05 | Insecticide means and method of making the active substance |
Country Status (37)
| Country | Link |
|---|---|
| US (1) | US4297361A (es) |
| JP (1) | JPS5925789B2 (es) |
| AT (1) | AT366886B (es) |
| AU (1) | AU531811B2 (es) |
| BE (1) | BE883348A (es) |
| BG (1) | BG34443A3 (es) |
| BR (1) | BR8003059A (es) |
| CA (1) | CA1136143A (es) |
| CH (1) | CH644601A5 (es) |
| CS (1) | CS216221B2 (es) |
| DD (1) | DD150840A5 (es) |
| DE (1) | DE2920183A1 (es) |
| DK (1) | DK211380A (es) |
| EG (1) | EG14276A (es) |
| ES (1) | ES491527A0 (es) |
| FI (1) | FI70889C (es) |
| FR (1) | FR2456737A1 (es) |
| GB (1) | GB2051052B (es) |
| GR (1) | GR67663B (es) |
| HU (1) | HU187276B (es) |
| IE (1) | IE49802B1 (es) |
| IL (1) | IL60080A (es) |
| IN (1) | IN154174B (es) |
| IT (1) | IT1140847B (es) |
| LU (1) | LU82457A1 (es) |
| MA (1) | MA18847A1 (es) |
| MX (1) | MX6405E (es) |
| NL (1) | NL8001920A (es) |
| NZ (1) | NZ193666A (es) |
| PL (1) | PL121559B1 (es) |
| PT (1) | PT71243A (es) |
| RO (1) | RO80087A (es) |
| SE (1) | SE8003465L (es) |
| SU (1) | SU902665A3 (es) |
| TR (1) | TR20541A (es) |
| YU (1) | YU41208B (es) |
| ZA (1) | ZA802923B (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4626543A (en) * | 1985-02-01 | 1986-12-02 | Shell Oil Company | Insecticidal 2,6-difluorobenzoyl derivatives of 4-substituted-1,3-thiazole-2-acetonitriles |
| EP0842931A4 (en) * | 1995-04-27 | 1998-09-02 | Nissan Chemical Ind Ltd | OXOPROPIONITRILE DERIVATIVES AND INSECT CONTROLLERS |
| ATE244219T1 (de) | 1996-04-25 | 2003-07-15 | Nissan Chemical Ind Ltd | Ethylenderivate und pestizide |
| DE19851986A1 (de) * | 1998-11-11 | 2000-05-18 | Bayer Ag | Phenyl-substituierte zyklische Enaminone |
| BR0016797A (pt) * | 1999-12-27 | 2002-11-05 | Nippon Soda Co | Composto, inseticida e acaricida |
| WO2001068589A1 (fr) * | 2000-03-17 | 2001-09-20 | Nippon Soda Co.,Ltd. | Composes acrylonitrile et agents pesticides |
| WO2002088099A1 (en) * | 2001-04-27 | 2002-11-07 | Nippon Soda Co.,Ltd. | Thiazolylcinnamonitrile compound and pest control agent |
| JPWO2003064401A1 (ja) * | 2002-01-29 | 2005-05-26 | 日本曹達株式会社 | アクリロニトリル化合物及び有害生物防除剤 |
| USD702103S1 (en) * | 2012-04-12 | 2014-04-08 | Qaid Zohar Zakiuddin Shahpurwala | Padlock |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1192701A (en) * | 1968-03-22 | 1970-05-20 | Ici Ltd | Novel Thiazole Derivatives, the preparation thereof and Compositions containing the same |
| US3769040A (en) * | 1970-11-09 | 1973-10-30 | Int Flavors & Fragrances Inc | Substituted thiazoles in flavoring processes and products produced thereby |
| US3637707A (en) * | 1970-11-24 | 1972-01-25 | Pfizer | 2-(substituted) 2-thiazolines for the control of rice blast |
| DE2703542C2 (de) * | 1977-01-26 | 1985-09-26 | Schering AG, 1000 Berlin und 4709 Bergkamen | Thiazolylzimtsäurenitrile, Insektenbekämpfungsmittel enthaltend diese Verbindungen sowie Verfahren zu ihrer Herstellung |
| DE2801794A1 (de) * | 1978-01-17 | 1979-07-19 | Basf Ag | Verfahren zur herstellung von thiazolderivaten und neue thiazole |
-
1979
- 1979-05-17 DE DE19792920183 patent/DE2920183A1/de not_active Ceased
-
1980
- 1980-04-01 NL NL8001920A patent/NL8001920A/nl not_active Application Discontinuation
- 1980-04-23 SU SU802912755A patent/SU902665A3/ru active
- 1980-04-29 YU YU1163/80A patent/YU41208B/xx unknown
- 1980-04-29 FI FI801379A patent/FI70889C/fi not_active IP Right Cessation
- 1980-04-29 IN IN318/DEL/80A patent/IN154174B/en unknown
- 1980-05-05 CS CS803122A patent/CS216221B2/cs unknown
- 1980-05-06 TR TR20541A patent/TR20541A/xx unknown
- 1980-05-08 CH CH363180A patent/CH644601A5/de not_active IP Right Cessation
- 1980-05-08 IT IT21877/80A patent/IT1140847B/it active
- 1980-05-08 SE SE8003465A patent/SE8003465L/xx not_active Application Discontinuation
- 1980-05-09 NZ NZ193666A patent/NZ193666A/xx unknown
- 1980-05-09 BG BG047700A patent/BG34443A3/xx unknown
- 1980-05-12 GB GB8015671A patent/GB2051052B/en not_active Expired
- 1980-05-12 MX MX808808U patent/MX6405E/es unknown
- 1980-05-13 AU AU58339/80A patent/AU531811B2/en not_active Ceased
- 1980-05-14 ES ES491527A patent/ES491527A0/es active Granted
- 1980-05-14 PT PT71243A patent/PT71243A/pt unknown
- 1980-05-14 DK DK211380A patent/DK211380A/da not_active Application Discontinuation
- 1980-05-14 FR FR8010870A patent/FR2456737A1/fr active Granted
- 1980-05-15 IL IL60080A patent/IL60080A/xx unknown
- 1980-05-15 PL PL1980224257A patent/PL121559B1/pl unknown
- 1980-05-15 DD DD80221139A patent/DD150840A5/de unknown
- 1980-05-15 GR GR61954A patent/GR67663B/el unknown
- 1980-05-16 CA CA000352129A patent/CA1136143A/en not_active Expired
- 1980-05-16 AT AT0263680A patent/AT366886B/de not_active IP Right Cessation
- 1980-05-16 BR BR8003059A patent/BR8003059A/pt unknown
- 1980-05-16 IE IE1018/80A patent/IE49802B1/en unknown
- 1980-05-16 JP JP55065200A patent/JPS5925789B2/ja not_active Expired
- 1980-05-16 ZA ZA00802923A patent/ZA802923B/xx unknown
- 1980-05-16 RO RO80101143A patent/RO80087A/ro unknown
- 1980-05-16 LU LU82457A patent/LU82457A1/de unknown
- 1980-05-16 BE BE0/200654A patent/BE883348A/fr not_active IP Right Cessation
- 1980-05-16 HU HU801229A patent/HU187276B/hu unknown
- 1980-05-17 EG EG303/80A patent/EG14276A/xx active
- 1980-05-17 MA MA19043A patent/MA18847A1/fr unknown
- 1980-05-19 US US06/151,109 patent/US4297361A/en not_active Expired - Lifetime
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69222746T2 (de) | Triazolopyrimidinderivate mit fungizider Aktivität | |
| DE69406538T2 (de) | Dihalotriazolopyrimidinderivate als fugizide | |
| JPH05186436A (ja) | ウラシル誘導体 | |
| EP0460575A1 (de) | Aromatische Verbindungen | |
| CS216221B2 (en) | Insecticide means and method of making the active substance | |
| CS214681B2 (en) | Fungicide means | |
| DE69110749T2 (de) | Barbitursäurederivate mit insektizider Wirkung. | |
| CS214830B2 (en) | Insecticide means and method of making the active substances | |
| DE1812761A1 (de) | Isoxazolylcarbamate,deren Mischungen,Verfahren zu deren Herstellung und deren Verwendung | |
| JPS59137480A (ja) | 有害生物防除組成物 | |
| EP0293743B1 (de) | Substituierte 5-Amino-Pyrazole und diese enthaltende Fungizide | |
| GB1564182A (en) | Benzothiazolone and benzoxazolone derivatives | |
| EP0033083B1 (de) | N,N-Dialkyl -0-(pyrazol-5-yl)-carbaminsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide | |
| JPS6084236A (ja) | アリ−ルメチルエ−テル誘導体、その製法及び該誘導体を含有する有害生物防除剤 | |
| KR840001148B1 (ko) | 티아졸일리덴-옥소-프로피오니트릴의 제조방법 | |
| DE3318648A1 (de) | Substituierte tetrahydrothiopyran-3,5-dion-4-carboxamide | |
| JPS6360736B2 (es) | ||
| EP0274988A2 (de) | Neue Dihydrothiadiazole | |
| JPH0733748A (ja) | ピリミジン誘導体および除草剤 | |
| CS244822B2 (en) | Agent for killing of insect and nematodes as theier larvae and eggs | |
| CH643563A5 (en) | 1,3-Diaza-2-phosphacyclohexane derivatives | |
| EP0350041B1 (en) | Esters of 2,2-dimethyl-cyclopropane-carboxylic acid | |
| KR830002202B1 (ko) | 아실-우레아의 제조방법 | |
| EP0067956A1 (de) | Heterocyclische Verbindungen, Verfahren zu deren Herstellung, Schädlingsbekämpfungsmittel, die diese Verbindungen als Wirkstoffe enthalten, sowie Verwendung solcher Verbindungen und Mittel zur Bekämpfung von Schädlingen | |
| JPH0660174B2 (ja) | ピラゾ−ルスルホニルウレア誘導体，その製法および該誘導体を含有する除草剤 |